2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl-(1→1')-2',4',6'-tri-O-acetyl-3'-azido-3'-deoxy-b-D-glucopyranoside | 1417719-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl-(1→1')-2',4',6'-tri-O-acetyl-3'-azido-3'-deoxy-b-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,5-diacetyloxy-4-azido-6-[(2R,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-azidooxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1417719-76-6
• 化学式: C₂₄H₃₂N₆O₁₅
• 分子量: 644.549
• InChiKey: DLKKSNGXXWVXED-ARYMTDNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  214
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl-(1→1')-2',4',6'-tri-O-acetyl-3'-azido-3'-deoxy-b-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到3-azido-3-deoxy-α-D-glucopyranosyl-(1→1')-3-azido-30-deoxy-b-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks

  摘要：

  Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1'-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose. The key alpha,beta-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1'-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.058
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-D-glucopyranose 在 乙酸铵 、 三氟甲磺酸三甲基硅酯 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl-(1→1')-2',4',6'-tri-O-acetyl-3'-azido-3'-deoxy-b-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks

  摘要：

  Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1'-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose. The key alpha,beta-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1'-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.058